Your Career Is Riskier Than You Think. Here's How To Manage It

#532: Joe McKay is an Australian business coach and solopreneur mentor who helps founders and solo business owners build thriving, opportunity-generating brands. After leaving a secure government job in Australia, Joe relocated his family to France, where he grew a six-figure solo business by overcoming his own fears of posting online and sharing his voice. Today, he specializes in helping busy founders and consultants create high-impact thought leadership content, while coaching solopreneurs to move from content to conversations to conversions. Joe’s clients have landed six-figure deals, booked keynote speaking engagements, guested on top podcasts, and secured board and advisory roles — all through the power of strategic content and personal brand growth.

#531 - Henna Pryor, CSP is a dynamic Workplace Performance Expert who speaks and writes about performance mindset, interpersonal dynamics, high-impact communication, and embracing bumps in a world that keeps optimizing for smoothness. She is a regular Expert Columnist for Inc. Magazine, 18x award-winning author of Good Awkward, and an in-demand global keynote speaker. Her playful personality and insightful talks blend 2 decades of working with corporate leaders and teams with a fresh, science-based approach to taking more strategic risks and boosting social and mental fitness for success at work. Her clients call her their “secret weapon for impossible change” — a title she wears proudly. In addition to speaking for TEDx, SXSW, and being frequently tapped by media outlets like Business.com, FastCompany, INSIDER, HuffPost, NBC, FOX, and more, she’s a SUCCESS Magazine Woman of Influence, LinkedIn Learning Instructor, and Glassdoor WorkLife Pro. Her book was also named a Kirkus Reviews’ Best Book of the Year.

#530: Katrina McGhee is a Career Break and Sabbatical Expert, creator of the Break Blueprint, BreakSpace and the author of Taking a Career Break for Dummies. As a certified master coach with an MBA, Katrina helps mid-career professionals create happier, more fulfilling lives by designing bold and transformational breaks. Her clients return from their breaks recharged, inspired, happily-employed and forever changed. On their time off, her 60+ clients have traveled the world, launched a business, changed careers and more. Katrina's work was inspired by her own 20-month career break where she saved $40,000 in just 18 months to quit her corporate job to travel the world. She's now an enthusiastic world traveler and digital nomad. Her advice on career breaks, money, and travel has been shared across various outlets including Forbes, Smarter Travel, Thrive Global, and Yahoo.

#529: Matt Doan is a transformational coach and entrepreneur dedicated to helping senior professionals break free from the constraints of corporate life and build sustainable, purpose-driven businesses online. After spending a decade climbing the corporate ladder in management consulting, he faced a personal crisis that forced him to reevaluate his path. Determined to reclaim his life, he immersed himself in entrepreneurship, coaching, and high-level mastermind programs, ultimately developing a proven system for transitioning from corporate roles to entrepreneurial freedom without unnecessary risk. Since 2019, Matt has guided hundreds of professionals through this life-changing journey, offering structured strategies and real-world insights to help them achieve autonomy, financial stability, and a fulfilling career beyond the traditional workforce.

#528: Sigute Zitikyte is a passionate advocate for multi-potentiality, helping ambitious individuals embrace their diverse interests and build careers that evolve with them. After spending a decade in the "multi-passionate shame cycle," feeling constrained by traditional career expectations, she broke free from a linear path and turned her creative pursuits into a thriving business. Through personal experience, she understands the struggle of balancing ambition with societal norms and now empowers others to confidently forge their own paths, integrating passion, purpose, and financial success. Sigute’s journey from the tech industry to entrepreneurship was fueled by a desire to live life on her own terms—one that values experiences as much as achievements. She now coaches multi-passionate professionals on building an online presence and expanding their income streams with clarity and confidence. By unlearning the need to conform and tuning into their inner voice, her clients gain the courage to create fulfilling careers beyond the conventional 9-to-5. Through her writing, coaching, and personal brand framework, Sigute inspires others to step boldly into their ambitions and craft a life they truly love.

#527: Kasey Jones is a renowned personal brand consultant, business growth strategist, and advocate for personal and professional empowerment. She specializes in transforming overworked and underpaid solopreneurs into profitable CEOs of businesses they love, using a bespoke blend of strategy, branding, systems, and mindset development. With nearly two decades of experience in early-stage growth strategy, B2B sales, demand generation, personal brand development, and relationship building at scale, Kasey excels at helping CEOs and C-suite executives amplify their unique strengths to drive business growth and build impactful brands. Over the years, Kasey has collaborated with startups like Sila, Ripcord, and Dealpoint (acquired by Clari), and has worked alongside brands such as Gwen Stefani’s GXVE, accelerators like PIE, and venture capital firms like True Venture Partners. Her expertise has guided hundreds of entrepreneurs, executives, and teams in finding their authentic voice, building authority, and reshaping their professional journeys to achieve more income, meaning, and purpose. Kasey’s guiding principles—empathy, generosity, resilience, honesty, and a commitment to doing the hard work—are at the core of her coaching philosophy. She believes in the power of authenticity and vulnerability, encouraging her clients to embrace their unique stories and transform them into powerful tools for connection and growth.

#526: Dr. Benjamin Ritter, founder of Live for Yourself (LFY) Consulting and award-winning author of "Becoming Fearless," is an international leadership and career coach, Sr. Talent Management Consultant, Top LinkedIn Voice, global speaker, and host of The Executive, and the Live Fearlessly Podcasts. Ben has coached over 500 leaders with a strong focus on senior-level executives across multiple industries and geographic regions, within organizations that varied in scale from 50 to over 250,000 employees and have included names such as Amazon, Coursera, DoorDash, Google, Fiserv, Northwestern, Mayo Clinic, Pinterest, Yelp, and more. Ben’s passions include working with Better for You CPG organizations, small business founders and minority-owned companies, for which he offers pro-bono coaching services. Ben possesses a Doctorate in Organizational Leadership with focus on value congruence and job satisfaction, an MBA in entrepreneurial management, and an MPH in health policy administration. Born and raised in Chicago, Illinois, Ben now resides in Austin, Texas, with his partner, Tiffany, Squirt, a “rebel in a shell” turtle, Elwood, a scruffy rescue pup, and Sima, the kitty queen of their kingdom.

#525: Nicole Greene is a Business and Lifestyle Strategist for badass women founders and executives who are committed to high performance in multiple non-negotiable roles (think executive, founder, mom, caretaker). Her actionable strategies and systems help these women step out of survival mode and achieve success, in life and business. Nicole’s passion for this work comes from her own experience making herself small (and eventually burning out) across a highly successful career, from defense intelligence to artisan chocolates, CPG and Health Tech, during which she founded three companies and built several others from Seed to Series B. Nicole describes herself as a recovering workaholic and forever high performer. She’s a classically-trained pastry chef, perpetual learner and dedicated mentor, as well as a mom of two boys (and an Australian Cattle Dog), living in Miami, FL. Nicole has a BA and MA from the University of Chicago and an MBA from the Kellogg School of Business at Northwestern University and is currently an Entrepreneur in Residence at the University of Miami.

#524: Brian Ondrako is, first and foremost, a dedicated Dad to an amazing young boy who keeps him energized and young at heart. As the host of the Just Get Started Podcast for over six years, Brian has built a platform for meaningful conversations and personal growth. Alongside his podcasting journey, he writes blogs three times a week, has published two children’s books with a third on the way, and serves as a Sales Mentor to B2B Founders and their teams. The past several years have been transformative for Brian, looking very different from the life he once knew. His current pursuits are rooted in a pivotal decision to take control of his life. Overcoming childhood challenges of poor confidence, low self-esteem, and a fear of judgment, Brian reshaped his path by embracing bravery, delayed gratification, and connecting with influential people. Through these steps, he discovered a sense of purpose that realigned his life's direction. Brian identifies as a NAVIGATOR, with his “North Star” guiding him to help others take control of their own lives. He believes that true fulfillment begins from within, by understanding that happiness is only achievable when we fully discover ourselves. As we explore who we are, Brian emphasizes, we uncover a COMPASS within us, one that guides us toward a more appreciative and purposeful life. This inner compass, according to Brian, forms the foundation for a happier and more fulfilling existence.

#523: Jason Silver is a multi-time founder of kids and a multi-time founder of companies. He gets his biggest thrill helping modern employees and their teams unlock a better way to work—surfing is a close second. He was an early employee at Airbnb and helped build an AI company from the ground up back before AI was the cool thing to do. Today, he advises a startup portfolio valued in the billions on how to build great, lasting companies that people actually enjoy working for. He’s a sought-after public speaker, instructor, and advisor on how to transform work into one of the biggest drivers of positivity in your life. When he’s not busy helping people solve their hardest workplace challenges, Jason’s kids are busy reminding him just how much of a work in progress he still is too.